Water → 8-Amino-1,2,3,4-tetrahydronaphthalen-2-ol

HRID 1984762Notes

Reaction equation

HRID 1984762 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH2:10][C:9](=[O:12])[CH2:8][CH2:7]2.[BH4-].[Na+].O>CO>[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH2:10][CH:9]([OH:12])[CH2:8][CH2:7]2

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 230669938-Amino-3,4-dihydro-1H-naphthalen-2-one

Product 1

HCID 230669958-Amino-1,2,3,4-tetrahydronaphthalen-2-olYield 71.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Next, to 8-amino-3,4-dihydronaphthalen-2(1H)-one (0.050 g, 0.318 mmol) in methanol (10 mL) was added sodium borohydride (0.030 g, 0.175 mmol) at 0° C., and the mixture was stirred for 1 hour. The mixture was poured into water, and the product was extracted with ethylacetate. The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure to afford 8-amino-1,2,3,4-tetra-hydronaphthalen-2-ol (0.037 g, 71% yield).

Workup

  1. extractionthe product was extracted with ethylacetate
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3f623aab00b446faac1947af66b0e84c
Source dataset
uspto-grants-2009_06
Patent number
US07544716B2

Reaction notes

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